US667861A - Process of producing chlorids of aromatic sulfonic acids. - Google Patents

Process of producing chlorids of aromatic sulfonic acids. Download PDF

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Publication number
US667861A
US667861A US2801400A US1900028014A US667861A US 667861 A US667861 A US 667861A US 2801400 A US2801400 A US 2801400A US 1900028014 A US1900028014 A US 1900028014A US 667861 A US667861 A US 667861A
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chlorids
sulfonic acids
producing
aromatic sulfonic
acid
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US2801400A
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Augustus Bischler
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BASLE CHEMICAL WORKS
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BASLE CHEMICAL WORKS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

Definitions

  • the orthotoluenesulfinic acid as well as the ethereal salts of the orthosulfinicbenzoic acid, is specially important for the preparation of the chlorids, by means of which the pure saccharin is directly obtained. 1 shall therefore only describe the process for the preparation of the products resulting from the abovementioned sultinic acids.
  • X stands for CH or OOOR, respectively, B being in alkyl group.
  • Example I Dissolve ten kilos of orthotoluenesulfinio acid in diluted caustic soda.
  • chlorin Into this solution chlorin is introduced until the formation of oily chlorid has ceased. Cool the solution which gets warm by the action of the chlorin, separate the orthotoluenesulfochlorid by decantation, and wash it with water.
  • the 0rthotoluenesulfochlorid is also obtained by mixing the above-mentioned solution of the sodium salt of the sulfinic acid with muriatic acid and by passing through the solution (containing sulfinic acid, which is partly dissolved and partly suspended) a strong current of chlorin. By the force of the current of chlorin the solution is more or less heated; but the temperature should be regulated so as not to surpass to centigrade.
  • Example II The methyl orthosulfinicbenzoate (melting-point 98 to 99 centigrade) obtained from the methylic ether of the anthranilic acid has to be dissolved in the necessary quantity of diluted alkali and must be treated with chlorid according to Example 1. Thus the orthosulfochlorid of methyl benzoate is obtained which Will melt at 64 to 65 Centigrade.
  • GEO GEO. GIrFoRD, AMAND BITTER.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

htlTlEH Status AUGUSTUS BISCHLER, OF BASLE, SWITZERLAND, ASSIGNOR TO BASLE CHEMICAL WORKS, OF SAME PLACE.
PROCESS OF PRODUCING CHLORIDS 0F AROMATIC SULFONIC ACIDS.
SPEGIFICATIDN formingpart of Letters Patent No. 667,861, dated February 12, 1901.
Application filed August 25.1900. Serial No. 28,014. (No specimens.)
To all 1071/0722 H; In/my concern.-
Be it known that I, AUGUSTUS BISCHLER, chemist and doctor of philosophy, a subject of the Emperor of Russia, and a resident of Basle, Switzerland, have in vented a new Prooess of Manufacturing Chloride of the Aromatic Sulfonic Acids, of which the following is a clear and complete specification.
I have found that the chlorids of the aromatic sulfonic acids may be obtained with ease and in a pure state by means of the aromatic sulfinic acids by treating these sulfinic acids as such or their salts with chlorin.
Among the aromatic sultinic acids the orthotoluenesulfinic acid, as well as the ethereal salts of the orthosulfinicbenzoic acid, is specially important for the preparation of the chlorids, by means of which the pure saccharin is directly obtained. 1 shall therefore only describe the process for the preparation of the products resulting from the abovementioned sultinic acids.
By passing chlorin in an aqueous solution of a salt of the orthotoluenesulfinic acid or of the ethereal salts of the orthosulfinicbenzoic acid the respective sulfochlorids are formed according to the following formula:
in which X stands for CH or OOOR, respectively, B being in alkyl group.
If the aqueous solutions of the salts of the sulfinic acids are liberated with mineral acids and chlorin is introduced into the suspension, the chlorids of the sulfonic acid are equally formed, besides the muriatic acid.
Example I: Dissolve ten kilos of orthotoluenesulfinio acid in diluted caustic soda.
Into this solution chlorin is introduced until the formation of oily chlorid has ceased. Cool the solution which gets warm by the action of the chlorin, separate the orthotoluenesulfochlorid by decantation, and wash it with water. The 0rthotoluenesulfochlorid is also obtained by mixing the above-mentioned solution of the sodium salt of the sulfinic acid with muriatic acid and by passing through the solution (containing sulfinic acid, which is partly dissolved and partly suspended) a strong current of chlorin. By the force of the current of chlorin the solution is more or less heated; but the temperature should be regulated so as not to surpass to centigrade.
Example II: The methyl orthosulfinicbenzoate (melting-point 98 to 99 centigrade) obtained from the methylic ether of the anthranilic acid has to be dissolved in the necessary quantity of diluted alkali and must be treated with chlorid according to Example 1. Thus the orthosulfochlorid of methyl benzoate is obtained which Will melt at 64 to 65 Centigrade.
Having thus described my invention, I claim- The herein-described process for producing chlorids of the aromatic sulfonic acids, which consists in treating the corresponding aromatic sulfinic acids with chlorin, substantially as set forth.
In witness whereof I have hereunto signed my name, this 11th day of August, 1900, in the presence of two subscribing Witnesses.
AUGUSTUS BISOHLER.
Witnesses:
GEO. GIrFoRD, AMAND BITTER.
US2801400A 1900-08-25 1900-08-25 Process of producing chlorids of aromatic sulfonic acids. Expired - Lifetime US667861A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3373192A (en) * 1959-08-20 1968-03-12 Continental Oil Co Preparation of alkane sulfonyl chlorides from trialkylaluminum and sulfuryl chloride
JP2011143727A (en) * 2004-05-12 2011-07-28 Woodbridge Foam Corp Vented mold and method for manufacturing molded article

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3373192A (en) * 1959-08-20 1968-03-12 Continental Oil Co Preparation of alkane sulfonyl chlorides from trialkylaluminum and sulfuryl chloride
JP2011143727A (en) * 2004-05-12 2011-07-28 Woodbridge Foam Corp Vented mold and method for manufacturing molded article

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